The perfume industry has a particular interest for compounds which are capable of prolonging the effect of active ingredients over a certain period of time, for example in order to overcome the problems encountered when using perfuming ingredients which are too volatile or have a poor substantivity. These compounds can be used in various applications, as for example in fine or functional perfumery. The washing of textiles is a particular field in which there is a constant quest to enable the effect of active substances, in particular perfumes, to be effective for a certain period of time after washing and drying. Indeed, many substances having fragrances which are particularly suitable for this type of application are, in fact, known to lack tenacity on laundry, or do not remain on the laundry when rinsed, with the result that their perfuming effect is experienced only briefly and not very intensely. Given the importance of this type of application in the perfume industry, research in this field has been sustained, in particular with the aim of finding new, and more effective solutions to the aforementioned problems.
Among the compounds of the present invention a few are known from the prior art. The compounds are 3-(phenylmethoxy)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone (by Fehr C et al. in Helv. Chim. Acta (1992), 75, 1023), 4-(phenylsulfonyl)-4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanone (by Torii S. et al. in Bull. Chem. Soc. Jpn. (1978), 51, 949), 4-(phenylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone (by Kuwajima I. et al. in Synthesis (1976), 602), 4-(phenylsulfonyl)-4-(2,6,6-trimethyl-1 or 2-cyclohexen-1-yl)-2-butanone (by Torii S. et al. in Chem. Lett. (1975), 479), 2-methyl-5-(1-methylethenyl)-3-[(4-methylphenyl)sulfonyl]-cyclohexanone (by Sayed A. et al. in Curr. Sci. (1999), 77, 818), 2-methyl-5-(1-methylethenyl)-3-(phenylmethoxy)-cyclohexanone (by Hareau G. et al. in J. Am. Chem. Soc. (1999), 121, 3640), 2-methyl-5-(1-methylethenyl)-3-(octylthio)-cyclohexanone (by Niyazymbetov M. et al. in Tetrahedron Lett. (1994), 35, 3037), 3,3′-thiobis[2-methyl-5-(1-methylethenyl)-cyclohexanone (Hargreaves M et al. in Z. Naturforsch., B: Anorg. Chem., Org. Chem. (1978), 33B, 1535), 2-methyl-5-(1-methylethenyl)-3-(phenylthio)-cyclohexanone and its optical isomers (e.g. by Bakuzis P et al. in J. Org. Chem. (1981), 46, 235), 4-(phenylsulfonyl)-4-(2,5,6,6-tetramethyl-1 or 2-cyclohexen-1-yl)-2-butanone and their optical isomers (by Torii S. et al. in J. Org. Chem. (1980), 45, 16), beta-[(4-methylphenyl)thio]-benzenepropanal (by Manickam G. et al. in Tetrahedron (1999), 55, 2721), beta-[4-(trifluoromethyl)phenoxy]-benzenepropanal (in ES 2103680), beta-(phenylsulfonyl)-benzenepropanal (by Vidal J. et al. in Tetrahedron Lett. (1986), 27, 3733), beta-(phenylmethoxy)-benzenepropanal (by Brickmann K. et al. in Chem. Ber. (1993), 126, 1227), beta-[[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]thio]-benzenepropanal (in EP 140298), beta-[(4-bromo-3-methylphenyl)thio]-benzenepropanal (by Loiseau P. et al. in Pharm. Acta Helv. (1983), 58, 115), beta-[(4-chlorophenyl)thio]-benzenepropanal (in FR 2509725), beta-[(4-methylphenyl)sulfonyl]-benzenepropanal (in WO 00/000198), and beta-(phenylthio)-benzenepropanal (e.g by Tilak B. et al. in Indian J. Chem. (1969), 7, 191).
All the compounds mentioned above have been used as synthetic intermediates, however, but not as perfuming ingredients. Moreover, in the documents mentioned hereinabove, there is no mention or suggestion of the potential use of the compounds as perfuming ingredients and more specifically of the use of such aid compounds to control the release of active, e.g. odoriferous, molecules.